How To Flirt

Presenting The Official AskMen Guide To Flirting Like A Pro

The AskMen Guide To Flirting

Most of us would like to be better at flirting. It seems as though the most expert flirters among us mingle effortlessly with the opposite sex (or whoever they're attracted to), while most of us blush, stumble over our words and generally fail to make an impression. Flirting requires a few key ingredients blended to perfection, including confidence, wit, flattery and respect, but often it seems like a gargantuan task to work up the nerve to talk to a woman, let alone seal the deal by charming her.

This difficulty helps to explain the meteoric rise of the self-styled pickup artist culture, which encourages shy and/or nerdy men to approach women by providing a few paint-by-numbers rules for gaining their attention. Unfortunately, these rules are based on shredding the self-esteem of the woman you’re flirting with, who is usually selected simply because she’s “a ten” (as in, scores 10/10 for looks.) The aim is to “neg” these women to bring them down a peg — issuing a kind of backhanded compliment calculated to unsettle her and make her insecure, and thus more grateful for your attention. This is an awful way to think about women, relationships and yourself. Pick up artists rely on an outmoded, market-based and sexist model of gender relations, and use unethical and ultimately ineffective strategies.

Yet pick up artists’ strategies remain popular because they tap into a desperate need for many men to find a way to confidently approach women. What we need, then, is an approach to flirting that contains some of the (few) useful ideas from pick up artist culture, but which isn't antisocial and rooted in damaging ideas about women and dating. Behold, then, some kinder, more effective flirting tips for the modern gentleman who doesn't condescend to or fear women, but would like to be better at flirting with them.

Let's break it down:

What Is Flirting?

In the simplest possible terms, flirting is usually a form of conversation that reveals a sexual or romantic attraction to another person, but which is lighthearted rather than serious in tone. It's usually the first step to elevating a platonic relationship into a romantic one, or to signal a romantic intention right off the bat.

Two of the best flirters in the game face off against each other.

To be good at flirting, and to engineer situations in which flirting is likely to be maximally effective, it’s important to consider the following points:

Choose The Right Environment

It's perfectly appropriate to flirt with single people in social environments where romantic approaches are customary, for example in bars and at parties. Of course, flirting on dating apps such as Tinder is appropriate, too.

However, there are other circumstances where flirting is not appropriate and should generally not be initiated. Flirting at work is never appropriate if you are in a position of power over your coworker (for example, if you are her boss), and in general you should not try to flirt with a co-worker during work hours — she’s trying to be professional! Situations when women are trying to go about their daily business, such as at the gym or on the bus or train, are not great times to approach her, either, as they are likely to be received as an annoyance rather than a compliment.

Work To Your Own Strengths

Lots of us would love to have Don Draper-levels of effortless charm, but if you're naturally a bit more goofy or shy than the smooth 1960s Mad Men (and women), forcing this persona is not going to work. Besides, it's unnecessary. Plenty of women prefer down-to-earth, funny and self-deprecating men and find the calculated slickness of more traditional flirters off-putting, so make sure that you’re flirting in a way that's natural to you and compatible with your personality type.

Shyness doesn't preclude you from having a successful flirting encounter. If you are shy, you will clearly have to build up the nerve to approach women — almost everyone finds this part somewhat difficult, by the way, even if they don't seem to! Fear not, though, because plenty of women find shy men endearing. Michael Cera is often used as a go-to example of an inept flirter — someone who’s hopelessly awkward and clueless with women — but some of my most dateable friends find find him irresistible. Somebody out there is bound to find your specific personality quirks endearing, so go for a funny, offbeat approach if that’s more your thing, rather than faking it.